Today, we’re thrilled to sit down with Simon Glairy, a renowned expert in insurance and Insurtech, with a deep focus on risk management and AI-driven risk assessment. With years of experience helping insurance carriers navigate complex transformations, Simon has a unique perspective on why product and go-to-market (GTM) initiatives often falter and how to steer them toward success. In this conversation, we explore the internal challenges that derail these initiatives, the impact of digital transformation on stakeholder expectations, and actionable strategies for building consensus across diverse teams. Join us as we uncover the hidden dynamics of organizational alignment and the keys to thriving in a rapidly evolving industry.
How do you see the main obstacles that cause product and GTM initiatives to fail at insurance carriers?
I think the biggest obstacles often come down to underestimating the internal decision-making journey. It’s rarely about the quality of the idea—insurance carriers have plenty of opportunities to innovate with pricing, packaging, or digital distribution. The real issue is a lack of alignment across teams. When stakeholders aren’t on the same page, even the most promising initiatives can stall before they launch. Miscommunication or differing priorities between finance, operations, distribution, and product teams can create roadblocks that are hard to overcome without deliberate effort to build consensus.
Can you tell us more about how internal alignment issues, like disagreements between departments, impact these initiatives?
Internal alignment issues are incredibly common and can be a silent killer for projects. I’ve seen cases where teams are working toward the same goal but with completely different assumptions. For instance, the product team might prioritize customer experience, while finance is laser-focused on immediate returns. If these perspectives aren’t reconciled early, you end up with delays, rework, or even complete halts. It’s not just about disagreement—it’s about the lack of a shared vision or a forum to hash out those differences before they derail the project.
Could you share a story of a project that didn’t succeed because of a lack of consensus among departments?
Absolutely. I worked with a carrier a few years back on a new digital quoting tool meant to streamline distribution. The product team was excited about enhancing broker efficiency, but the operations team flagged major integration issues with existing systems, and finance wasn’t convinced the upfront cost would pay off quickly enough. Without a unified plan or early dialogue, each group dug into their position. The project dragged on for months before leadership finally pulled the plug. It was a hard lesson in the need to bring everyone to the table from day one to align on goals and constraints.
When launching a new initiative, how do you manage the competing priorities of stakeholders like the CFO, COO, distribution, and product teams?
Managing competing priorities starts with understanding each stakeholder’s lens. I make it a point to map out what drives each group—whether it’s ROI for the CFO, execution feasibility for the COO, market fit for distribution, or risk balance for product. Then, I facilitate conversations to find common ground. It often involves translating one team’s concerns into another’s language, like showing finance how operational efficiencies can lead to long-term gains. Building trust and creating a shared narrative around the initiative’s value is key to getting everyone pulling in the same direction.
What concerns does the CFO typically bring up about new product or GTM plans, and how do you address them?
CFOs are usually focused on the numbers—how soon will this impact the bottom line or improve the combined ratio? They’re skeptical of big investments in tech or digital tools without a clear payback story. I tackle this by building a solid ROI case upfront, using data on customer willingness to pay or projected operational savings. I also emphasize quick wins alongside long-term benefits to show that the initiative isn’t just a gamble. Transparency about risks and timelines helps build credibility with them.
How do operations teams generally respond to new digital tools or pricing changes, and what hurdles have you faced in gaining their support?
Operations teams are all about execution, so their primary concern is whether the current systems and processes can handle the change. I’ve seen resistance when new digital tools or pricing structures seem to add complexity or risk, like potential downtime during integration. The hurdle is often fear of the unknown. I address this by involving them early, walking through how the changes will work day-to-day, and highlighting benefits like reduced manual work. Pilot programs can also help, letting them test the waters before a full rollout.
What strategies do you use to get distribution teams, like brokers or agents, on board with new packaging or digital approaches?
Distribution teams are critical because they’re the bridge to the customer. If they’re not bought in, adoption suffers. I’ve found success by involving them early in the design phase—gathering their input on packaging or digital tools through focus groups or one-on-one chats. When they feel heard, resistance drops. I also focus on showing how the changes make their jobs easier, like faster quoting or better customer insights. It’s about empowering them, not disrupting their workflow, so they see the initiative as a win for their business too.
How has digital transformation shifted the expectations around planning and executing product and GTM initiatives for different stakeholders?
Digital transformation has raised the bar across the board. For finance, real-time analytics mean they expect precise ROI projections almost instantly. Operations teams now face new governance challenges with cloud systems or API integrations, shifting their focus from legacy constraints to managing digital risks. Distribution teams need to adapt to new channels like embedded insurance, while product teams grapple with balancing personalization and simplicity. Overall, digital tools create more opportunities but also more scrutiny—everyone expects faster, data-driven decisions, and that puts pressure on how initiatives are planned and rolled out.
What advice do you have for our readers who are looking to drive successful product or GTM initiatives in their own organizations?
My advice is to prioritize alignment over everything else. Before diving into tech or strategy, map out your stakeholders and understand their priorities. Build a shared vision by connecting the dots between growth, efficiency, and customer value. Don’t shy away from tough conversations early—they save time later. And remember, transformation isn’t just about tools; it’s about people. Invest in communication, transparency, and small wins to build momentum. If you can get your teams rowing in the same direction, even the boldest initiatives have a real shot at success.
